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Synfacts 2006(3): 0192-0192  
DOI: 10.1055/s-2006-931922
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of rac-Garsubellin A

Contributor(s): Philip Kocienski
A. Kuramochi, H. Usuda, K. Yamatsugu, M. Kanai*, M. Shibasaki*
University of Tokyo, Japan
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Garsubellin A is polyprenylated phloroglucin isolated from Garcinia subelliptica. It has potent neurotrophic activity owing to its inhibition of choline acetyltransferase. The main challenge in the synthesis is the construction of the two highly congested stereogenic centers at C4 and C6. The synthesis is linear (23 steps) and delivers a racemic product. An asymmetric variant using a Koga alkylation to install the prenyl substituent in A is in progress.